Thanks to all for your thoughtful and cogent words.
That Catalina 25 *kinda* calls to me. It doesn't scream, but the PO's care of it is evident, and most of the right stuff has been replaced: internal and mast wiring, etc. The teak is immaculate and the bottom paint is good. My only worry is that I might find 25' too small. Plenty enough room for our family of three, but the pop-top seems like it wouldn't be great for added guests, as I figure nobody should sit on top of it. I also worry about it handling rougher seas like some ~3ft ones I saw this summer coming home across the Sound in the evening. I figure I could maybe get it for $10k (13.5k asking price) by leveraging some comps. I'd have that "pride of ownership" and ability to sail at will. I think I might always be "what-if"ing myself regarding a larger boat, though, and it'd be nice to have more main-cabin berthing without building a custom insert.
I do want the ability to do a week-long cruise through the Sound, maybe with another couple/family, but that'll be maybe a yearly thing, so maybe I could just charter a bigger boat for that, and stick with the smaller, affordable one for daysails.
My wife has said that she could take care of our son some weekends while I go out with other folks (no shortage of crew/passengers via the local Meetup), but I think I need to be realistic about how much of that I'd be doing in the next year, especially if my work schedule needs to flex into the weekends since I'll be home with him during the days. I also need to face the fact that we have credit card debt, a probable sewer assessment in the next year, and an ELOC that's currently only getting interest payments. Thus, as Jody suggests, maybe I should hold off on any purchase just yet. I've felt compelled to take advantage of the current depression in prices, ostensibly due to the economic situation, and I guess the season -- more boats seem to come onto the market in the fall, and people sell for less because they don't want to pay moorage because they're warm-weather-only sailors. If six months or a year from now prices are generally 30%+ higher than they are right now, I'll be kicking myself.
If that C25 http://seattle.craigslist.org/see/boa/838069505.html
were a C27 in the same shape, or maybe even a tall rig C25, I might be less ambivalent. Maybe something like this is what I should be thinking about instead for a potential 2009 purchase: 1983 Catalina 27 Tall Rig Cruiser
I've read here that many of you have done hardware rebedding, complete rewiring, etc. on your boats, and while I envy your skills, I have to be honest with myself that I'd have to hire a pro to do anything on my boat past cleaning and fueling - and that factors into the cost.
In the meantime maybe I should be practical and just join Windworks' club in the spring. I could do daysails for as little as $74 incremental cost and maybe do some teaching with my wife, once I get her on a boat more stable than the J24 that's all she's known so far. Because as many of you know, the sailing thing works out much, much better with spousal participation.
These past five months living close to the water again but without primary access to a boat have been frustrating. Each day we have wind I turn to my wife and sigh about how we should be on the water. Le Sigh.